04/12/2013 10:05 am ET

David Letterman Interview: The Host's Most Memorable Moments On His 66th Birthday

On his 66th birthday, David Letterman seems to be in the news more than ever.

Letterman made headlines this week after making troubled star Lindsay Lohan cry on his late night show. While Letterman grilled Lohan about her addictions and upcoming trip to rehab, she ultimately shed tears when he praised her for appearing on his show, despite the fact that she is often the butt of his jokes.

“We never thought we’d see you again honestly, because of the jokes and stuff. And yet, you have enough spine, enough sense of yourself, enough poise to come out here and talk to me,” said Letterman.

Some felt that Letterman was being cruel by grilling Lohan about uncomfortable topics, while others praised him for his earnestness. Either way, it was certainly a memorable interview.

Of course, the comedian has conducted many unforgettable interviews over the years, a feat which we want to honor on his birthday. From the hilarious, to the uncomfortable, to the downright perplexing, below we have compiled a slideshow of Letterman’s most memorable interviews with Hollywood celebrities.

Happy birthday Dave! May you reign over late night for years to come.

David Letterman's Top Interviews